RU2018122936A - METHOD FOR CLEANING A PETROZYRENE DERIVATIVE, ITS CRYSTAL FORM AND METHOD FOR PRODUCING CRYSTAL FORM - Google Patents

METHOD FOR CLEANING A PETROZYRENE DERIVATIVE, ITS CRYSTAL FORM AND METHOD FOR PRODUCING CRYSTAL FORM Download PDF

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RU2018122936A
RU2018122936A RU2018122936A RU2018122936A RU2018122936A RU 2018122936 A RU2018122936 A RU 2018122936A RU 2018122936 A RU2018122936 A RU 2018122936A RU 2018122936 A RU2018122936 A RU 2018122936A RU 2018122936 A RU2018122936 A RU 2018122936A
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crystalline form
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compound
solid
solution
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RU2729074C2 (en
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Чже-Чхон РЮ
Ён-Кён ПАК
Хён-Кю КИМ
Дон-Ёп СИН
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Ханлим Фармасьютикал Ко., Лтд.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Claims (28)

1. Способ очистки соединения с формулой 1, включающий преобразование сырого соединения с формулой 1 в его кристаллическую форму1. A method of purifying a compound of formula 1, comprising converting a crude compound of formula 1 into its crystalline form
Figure 00000001
.
Figure 00000001
. 2. Способ по п. 1, в котором сырое соединение с формулой 1 представляет собой соединение в аморфной форме.2. The method of claim 1, wherein the crude compound of formula 1 is a compound in amorphous form. 3. Способ по п. 1, в котором кристаллическая форма представляет собой кристаллическую форму А соединения с формулой 1 с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 19,06 и 26,48°.3. The method according to p. 1, in which the crystalline form is a crystalline form A of the compounds of formula 1 with a debris PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 19.06 and 26.48 °. 4. Способ по п. 1, в котором кристаллическая форма представляет собой кристаллическую форму А соединения с формулой 1 с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 16,48, 17,89, 18,89, 19,06, 19,31 и 26,48°.4. The method according to p. 1, in which the crystalline form is a crystalline form A of the compounds of formula 1 with a debris PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 16.48, 17.89, 18.89, 19.06, 19.31 and 26.48 °. 5. Способ по п. 1, в котором кристаллическая форма представляет собой кристаллическую форму А соединения с формулой 1 с термограммой дифференциальной сканирующей калориметрии (ДСК) с эндотермическим пиком между 240°С и 250°С.5. The method according to p. 1, in which the crystalline form is a crystalline form A of the compounds of formula 1 with a differential scanning calorimetry (DSC) thermogram with an endothermic peak between 240 ° C and 250 ° C. 6. Способ по п. 1, в котором кристаллическая форма представляет собой кристаллическую форму А соединения с формулой 1 с термограммой термогравиметрического анализа (ТГА) с потерей веса между 300°С и 310°С.6. The method according to p. 1, in which the crystalline form is a crystalline form A of the compounds of formula 1 with thermogram of thermogravimetric analysis (TGA) with a weight loss between 300 ° C and 310 ° C. 7. Кристаллическая форма соединения с формулой 17. The crystalline form of the compounds with formula 1
Figure 00000001
.
Figure 00000001
. 8. Кристаллическая форма по п. 7, в которой кристаллическая форма соединения с формулой 1 представляет собой кристаллическую форму А с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 19,06 и 26,48.8. The crystalline form according to claim 7, in which the crystalline form of the compound with formula 1 is crystalline form A with a debris pattern of PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 19.06 and 26.48. 9. Кристаллическая форма по п. 7, в которой кристаллическая форма соединения с формулой 1 представляет собой кристаллическую форму А с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 16,48, 17,89, 18,89, 19,06, 19,31 и 26,48.9. The crystalline form according to claim 7, in which the crystalline form of the compound of formula 1 is crystalline form A with a debris pattern of PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 16.48 , 17.89, 18.89, 19.06, 19.31 and 26.48. 10. Кристаллическая форма по п. 7, в которой кристаллическая форма соединения с формулой 1 представляет собой кристаллическую форму А с термограммой дифференциальной сканирующей калориметрии (ДСК) с эндотермическим пиком между 240°С и 250°С.10. The crystalline form of claim 7, wherein the crystalline form of the compound of formula 1 is crystalline Form A with a differential scanning calorimetry (DSC) thermogram with an endothermic peak between 240 ° C and 250 ° C. 11. Кристаллическая форма по п. 7, в которой кристаллическая форма соединения с формулой 1 представляет собой кристаллическую форму А с термограммой термогравиметрического анализа (ТГА) с потерей веса между 300 °С и 310 °С.11. The crystalline form according to claim 7, wherein the crystalline form of the compound of formula 1 is crystalline form A with a thermogram of thermogravimetric analysis (TGA) with a weight loss of between 300 ° C. and 310 ° C. 12. Способ получения кристаллической формы соединения с формулой 1, включающий растворение аморфного соединения с формулой 1 в органическом растворителе для получения раствора; перемешивание, дистилляцию или охлаждение раствора с образованием твердого вещества или дистиллята, последующее охлаждение раствора с образованием твердого вещества и выделение твердого вещества12. A method of obtaining a crystalline form of a compound of formula 1, comprising dissolving an amorphous compound of formula 1 in an organic solvent to obtain a solution; mixing, distilling or cooling the solution to form a solid or distillate, then cooling the solution to form a solid and isolating the solid
Figure 00000001
.
Figure 00000001
. 13. Способ по п. 12, в котором органический растворитель представляет собой один или несколько растворителей, выбранных из группы, состоящей из метанола, этанола, изопропанола, ацетона, метилэтилкетона, ацетонитрила, этилацетата, дихлорметана, тетрагидрофурана, диметилсульфоксида, диметилформамида и N-метил-2- пирролидона.13. The method according to p. 12, in which the organic solvent is one or more solvents selected from the group consisting of methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, acetonitrile, ethyl acetate, dichloromethane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide and N-methyl -2-pyrrolidone. 14. Способ получения кристаллической формы соединения с формулой 1, включающий растворение аморфного соединения с формулой 1 в органическом растворителе для получения раствора; добавление раствора в антирастворитель для получения твердого вещества или добавление антирастворителя в раствор для получения твердого вещества и выделение твердого вещества14. A method of obtaining a crystalline form of a compound of formula 1, comprising dissolving an amorphous compound of formula 1 in an organic solvent to obtain a solution; adding a solution to an anti-solvent to obtain a solid or adding an anti-solvent to a solution to obtain a solid and isolating a solid
Figure 00000001
.
Figure 00000001
. 15. Способ по п. 14, в котором органический растворитель представляет собой один или несколько растворителей, выбранных из группы, состоящей из метанола, этанола, изопропанола, ацетона, метилэтилкетона, ацетонитрила, этилацетата, дихлорметана, тетрагидрофурана, диметилсульфоксида, диметилформамида и N-метил-2- пирролидона.15. The method according to claim 14, in which the organic solvent is one or more solvents selected from the group consisting of methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, acetonitrile, ethyl acetate, dichloromethane, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide and N-methyl -2-pyrrolidone. 16. Способ по п. 14, в котором антирастворитель представляет собой один или несколько антирастворителей, выбранных из группы, состоящей из воды, гексана, гептана, диэтилового эфира, изопропилового эфира, ди-н-бутилового эфира и толуола.16. The method according to p. 14, in which the anti-solvent is one or more anti-solvents selected from the group consisting of water, hexane, heptane, diethyl ether, isopropyl ether, di-n-butyl ether and toluene. 17. Способ получения кристаллической формы соединения с формулой 1, включающий растворение аморфного соединения с формулой 1 в воде посредством добавления в нее кислоты для получения раствора; добавление основания в раствор для получения твердого вещества и выделение твердого вещества17. A method of obtaining a crystalline form of a compound of formula 1, comprising dissolving an amorphous compound of formula 1 in water by adding acid to it to form a solution; adding a base to the solid solution and isolating the solid
Figure 00000001
.
Figure 00000001
. 18. Способ по п. 17, в котором кислота представляет собой одну или несколько кислот, выбранных из группы, состоящей из хлористоводородной кислоты, уксусной кислоты и муравьиной кислоты.18. The method of claim 17, wherein the acid is one or more acids selected from the group consisting of hydrochloric acid, acetic acid, and formic acid. 19. Способ по п. 17, в котором основание представляет собой одно или несколько оснований, выбранных из группы, состоящей из гидроксида натрия, гидроксида калия, бикарбоната натрия и карбоната натрия.19. The method according to p. 17, in which the base is one or more bases selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium bicarbonate and sodium carbonate. 20. Способ по любому из пп. 12-19, в котором кристаллическая форма соединения с формулой 1 представляет собой кристаллическую форму А с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 19,06 и 26,48°.20. The method according to any one of paragraphs. 12-19, in which the crystalline form of the compound with formula 1 is crystalline form A with a debris diagram of the PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 19.06 and 26.48 ° . 21. Способ по любому из пп. 12-19, в котором кристаллическая форма представляет собой кристаллическую форму А с дебаеграммой ПРД с пиками 2θ ± 0,2°2θ на 12,27, 12,65, 16,07, 16,48, 17,89, 18,89, 19,06, 19,31 и 26,48.21. The method according to any one of paragraphs. 12-19, in which the crystalline form is a crystalline form A with a debris pattern of PRD with peaks of 2θ ± 0.2 ° 2θ at 12.27, 12.65, 16.07, 16.48, 17.89, 18.89, 19.06, 19.31 and 26.48. 22. Способ по любому из пп. 12-19, в котором кристаллическая форма представляет собой кристаллическую форму А с термограммой дифференциальной сканирующей калориметрии (ДСК) с эндотермическим пиком между 240°С и 250°С.22. The method according to any one of paragraphs. 12-19, in which the crystalline form is crystalline form A with a differential scanning calorimetry (DSC) thermogram with an endothermic peak between 240 ° C and 250 ° C. 23. Способ по любому из пп. 12-19, в котором кристаллическая форма представляет собой кристаллическую форму А с термограммой термогравиметрического анализа (ТГА) с потерей веса между 300°С и 310°С. 23. The method according to any one of paragraphs. 12-19, in which the crystalline form is crystalline form A with a thermogram of thermogravimetric analysis (TGA) with a weight loss between 300 ° C and 310 ° C.
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